(2S,3R,4E)-2-(hexadecanoylamino)-4-eicosene-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-2-(hexadecanoylamino)-4-eicosene-1,3-diol
• 英文别名: N-(hexadecanoyl)-4E-eicosasphingenine；N-[(E,2S,3R)-1,3-dihydroxyicos-4-en-2-yl]hexadecanamide
• 化学式: C₃₆H₇₁NO₃
• 分子量: 565.965
• InChiKey: JIPDEQIFHUXXAB-NXCSZAMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  40
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3R,4E)-2-氨基-4-二十碳烯-1,3-二醇 、 棕榈酰氯 在 吡啶 、 N-甲基吡咯烷酮 、 p-OH-m-NO₂-C₆H₃-C(O)-resin 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R,4E)-2-(hexadecanoylamino)-4-eicosene-1,3-diol
  参考文献：
  名称：

  Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells

  摘要：

  Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4(+) T cells, is an important stimulus for the switch of the antibody isotype to IgE in both mice and humans. In this study we investigated the inhibitory activity of IL-4 production in activated T cells by screening ceramide derivatives prepared by solid phase combinatorial chemistry. Many ceramide derivatives significantly inhibited IL-4 production in T cells. In particular, ceramide derivatives with a lauroyl group showed strong inhibitory activities on IL-4 production in both phorbol 12-myristate 13-acetate (PMA)-activated EL4 T cells and antigen-primed cells, suggesting that they can be used as compounds for the development of anti-allergic agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.027

文献信息

• Mutant endoglycoceramidases with enhanced synthetic activity
  申请人：La Jolla Pharmaceutical Company

  公开号：US10294504B2

  公开（公告）日：2019-05-21

  The present invention relates to a novel endoglycoceramidase whose hydrolytic activity has been substantially reduced or eliminated, such that the enzyme is useful for synthesis of glycolipids from a monosaccharide or oligosaccharide and a ceramide. More specifically, the endoglycoceramidase is a mutant version of a naturally occurring endoglycoceramidase, preferably comprising a mutation within the active site or the nucleophilic site of the enzyme and more preferably comprising a substitution mutation of the Glu residue within the active site or the nucleophilic site. Also disclosed are a method for generating the mutant endoglycoceramidase and a method for enzymatically synthesizing glycolipids using this mutant enzyme.

  本发明涉及一种新型内聚甘糖苷酶，其水解活性已大大降低或消除，因此该酶可用于由单糖或寡糖和神经酰胺合成糖脂。更具体地说，内糖化酶是天然存在的内糖化酶的突变体，优选包括酶的活性位点或亲核位点内的突变，更优选包括活性位点或亲核位点内 Glu 残基的取代突变。还公开了一种产生突变型内糖化酶的方法和一种使用这种突变型酶酶解合成糖脂的方法。
• Mutant Endoglycoceramidases With Enhanced Synthetic Activity
  申请人：Johnson Karl F.

  公开号：US20090170155A1

  公开（公告）日：2009-07-02

  The present invention relates to a novel endoglycoceramidase whose hydrolytic activity has been substantially reduced or eliminated, such that the enzyme is useful for synthesis of glycolipids from a monosaccharide or oligosaccharide and a ceramide. More specifically, the endoglycoceramidase is a mutant version of a naturally occurring endoglycoceramidase, preferably comprising a mutation within the active site or the nucleophilic site of the enzyme and more preferably comprising a substitution mutation of the Glu residue within the active site or the nucleophilic site. Also disclosed are a method for generating the mutant endoglycoceramidase and a method for enzymatically synthesizing glycolipids using this mutant enzyme.
• SOLVENTS FOR MUTANT ENDOGLYCOCERAMIDASES WITH SYNTHETIC ACTIVITY
  申请人：Defrees Shawn

  公开号：US20090176278A1

  公开（公告）日：2009-07-09

  The present invention provides reaction mixtures comprising a solvent having at least one of an alkoxy ether and/or a polyhydric alcohol for use in reactions with a mutant endoglycoceramidase having enhanced synthetic activity.
• MUTANT ENDOGLYCOCERAMIDASES WITH ENHANCED SYNTHETIC ACTIVITY
  申请人：Johnson Karl F.

  公开号：US20140147891A1

  公开（公告）日：2014-05-29

  The present invention relates to a novel endoglycoceramidase whose hydrolytic activity has been substantially reduced or eliminated, such that the enzyme is useful for synthesis of glycolipids from a monosaccharide or oligosaccharide and a ceramide. More specifically, the endoglycoceramidase is a mutant version of a naturally occurring endoglycoceramidase, preferably comprising a mutation within the active site or the nucleophilic site of the enzyme and more preferably comprising a substitution mutation of the Glu residue within the active site or the nucleophilic site. Also disclosed are a method for generating the mutant endoglycoceramidase and a method for enzymatically synthesizing glycolipids using this mutant enzyme.
• Mutant Endoglycoceramidases with Enhanced Synthetic Activity
  申请人：Seneb Biosciences, Inc.

  公开号：US20160032342A1

  公开（公告）日：2016-02-04

  The present invention relates to a novel endoglycoceramidase whose hydrolytic activity has been substantially reduced or eliminated, such that the enzyme is useful for synthesis of glycolipids from a monosaccharide or oligosaccharide and a ceramide. More specifically, the endoglycoceramidase is a mutant version of a naturally occurring endoglycoceramidase, preferably comprising a mutation within the active site or the nucleophilic site of the enzyme and more preferably comprising a substitution mutation of the Glu residue within the active site or the nucleophilic site. Also disclosed are a method for generating the mutant endoglycoceramidase and a method for enzymatically synthesizing glycolipids using this mutant enzyme.